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Homochirality

About: Homochirality is a research topic. Over the lifetime, 814 publications have been published within this topic receiving 28034 citations.


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Journal ArticleDOI
28 Dec 1995-Nature
TL;DR: In this paper, it was shown that autocatalysis in a chemical reaction can indeed enhance a small initial enantiomeric excess of a chiral molecule, and that the resulting chirality imbalance can become overwhelming.
Abstract: THE homochirality of natural amino acids and sugars remains a puzzle for theories of the chemical origin of life1–18. In 1953 Frank7 proposed a reaction scheme by which a combination of autocatalysis and inhibition in a system of replicating chiral molecules can allow small random fluctuations in an initially racemic mixture to tip the balance to yield almost exclusively one enantiomer. Here we show experimentally that autocatalysis in a chemical reaction can indeed enhance a small initial enantiomeric excess of a chiral molecule. When a 5-pyrimidyl alkanol with a small (2%) enantiomeric excess is treated with diisopropylzinc and pyrimidine-5-car-boxaldehyde, it undergoes an autocatalytic reaction to generate more of the alkanol. Because the reaction involves a chiral catalyst generated from the initial alkanol, and because the catalytic step is enantioselective, the enantiomeric excess of the product is enhanced. This process provides a mechanism by which a small initial imbalance in chirality can become overwhelming.

861 citations

Journal ArticleDOI
16 Nov 1990-Science
TL;DR: This result represents an experimental demonstration of chiral symmetry breaking or total spontaneous resolution on a macroscopic level brought about by autocatalysis and competition between L- and D-crystals.
Abstract: Sodium chlorate (NaClO3) crystals are optically active although the molecules of the compound are not chiral. When crystallized from an aqueous solution while the solution is not stirred, statistically equal numbers of levo (L) and dextro (D) NaClO3 crystals were found. When the solution was stirred, however, almost all of the NaClO3 crystals (99.7 percent) in a particular sample had the same chirality, either levo or dextro. This result represents an experimental demonstration of chiral symmetry breaking or total spontaneous resolution on a macroscopic level brought about by autocatalysis and competition between L- and D-crystals.

774 citations

Journal ArticleDOI
14 Feb 1997-Science
TL;DR: Gas chromatographic-mass spectral analyses of the four stereoisomers of 2-amino-2,3-dimethylpentanoic acid obtained from the Murchison meteorite show that the L enantiomer occurs in excess, indicative of an asymmetric influence on organic chemical evolution before the origin of life.
Abstract: Gas chromatographic-mass spectral analyses of the four stereoisomers of 2-amino-2,3-dimethylpentanoic acid (dl-alpha-methylisoleucine and dl-alpha-methylalloisoleucine) obtained from the Murchison meteorite show that the L enantiomer occurs in excess (7.0 and 9.1%, respectively) in both of the enantiomeric pairs. Similar results were obtained for two other alpha-methyl amino acids, isovaline and alpha-methylnorvaline, although the alpha hydrogen analogs of these amino acids, alpha-amino-n-butyric acid and norvaline, were found to be racemates. With the exception of alpha-amino-n-butyric acid, these amino acids are either unknown or of limited occurrence in the biosphere. Because carbonaceous chondrites formed 4.5 billion years ago, the results are indicative of an asymmetric influence on organic chemical evolution before the origin of life.

768 citations

Journal ArticleDOI
20 May 2004-Nature
TL;DR: These findings could lead to new uses for mesoporous silica and other chiral pore materials in, for example, catalysis and separation media, where both shape selectivity and enantioselectivity can be applied to the manufacturing of enantiomerically pure chemicals and pharmaceuticals.
Abstract: Chirality is widely expressed in organic materials, perhaps most notably in biological molecules such as DNA, and in proteins, owing to the homochirality of their components (d-sugars and l-amino acids). But the occurrence of large-scale chiral pores in inorganic materials is rare1. Although some progress has been made in strategies to synthesize helical and chiral zeolite-like materials1,2,3, the synthesis of enantiomerically pure mesoporous materials is a challenge that remains unsolved4. Here we report the surfactant-templated synthesis of ordered chiral mesoporous silica, together with a general approach for the structural analysis of chiral mesoporous crystals by electron microscopy. The material that we have synthesized has a twisted hexagonal rod-like morphology, with diameter 130–180 nm and length 1–6 µm. Transmission electron microscopy combined with computer simulations confirm the presence of hexagonally ordered chiral channels of 2.2 nm diameter winding around the central axis of the rods. Our findings could lead to new uses for mesoporous silica and other chiral pore materials in, for example, catalysis and separation media, where both shape selectivity and enantioselectivity5 can be applied to the manufacturing of enantiomerically pure chemicals and pharmaceuticals.

694 citations

Journal ArticleDOI
TL;DR: Biomolecular homochirality, the origin of which is still a puzzle, has challenged scientists to design chemical systems that provide chiral molecules through absolute asymmetric synthesis and to amplify a small stereochemical bias in such systems.
Abstract: Biomolecular homochirality, the origin of which is still a puzzle, has challenged scientists to design chemical systems that provide chiral molecules through absolute asymmetric synthesis and to amplify a small stereochemical bias in such systems. The photoresolution of the enantiomers of helical-shaped, sterically overcrowded alkene 1 with circularly polarized light and the transduction of the stereochemical information by triggering the helical arrangement of a large collection of achiral molecules in a twisted nematic liquid crystalline phase (2) are examples of control and amplification of chirality.

643 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202342
202266
202150
202039
201947
201830